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Danny Quinn, a former "street kid" from Southie, returns home from New York City a new man, only to find his mother overwhelmed with worry as her other three kids are caught up in the madness of the hardscrabble neighborhood in which drinking, fucking and fighting is the way of life. Concerned for his mother, Danny tracks down his brothers only to find out they're deeply embedded in the life he left behind. His brothers are in debt to local mobster Colie Powers, his younger sister Kathy has become a barfly. For his mother's sake, Danny must get his hands on some quick cash in order to stop his brothers from getting their legs broken and his sister off the streets. In his pursuit to help his ailing mother and right his family's name on the streets of Soutie, Danny crosses paths with his old girlfriend Maryann, finding the love he left behind has only blossomed when the two soul mates find themselves alone. She tells how she heard about the gunfight he was in with Joey Ward and wants to know if that's why he left town. Danny confesses that real reason he left town was that he needed to change if he were to become the man that she would want him to be. Knowing he has business to take care of and not wanting to drag Maryann into it, he leaves. Two of his old pals know Danny needs money and offer him an opportunity to be a partner in an underground gambling club, they neglect to tell Danny that their silent partner is his old nemesis, Joey Ward. It doesn't take long before Danny finds out and he and Joey are face to face. It takes all the strength Danny can muster not to beat the living hell out of Joey and he declares to his friends that once he gets the money he needs to help his family, he's out of the gambling business for good. In Danny's absence from the neighborhood, Joey's father Butchie has declared war on Colie Powers and without knowing this Danny finds himself caught up in the middle of their war as it looks like he's in business with the Wards. Before Danny knows it, Joey makes a power move with the intention of screwing him and his friends. Joey kills one of Danny's friends and now he must do what it takes before he's next.

Southie was originally written as "Brass Ring" by two young screenwriters from Boston, James Cummings and Dave McLaughlin. Cummings was born in Southie and left Boston with the hopes of becoming an actor. After several years of studying with George Loros and struggling to break into the business, Loros told Cummings that if he wanted to be in show business he needed to create his own work. He took those words to heart and began producing stage plays from the money he made as the doorman at the well-known bar in the lower east side of Manhattan, NW3. After taking a few weeks off in the summer of '93, Cummings went home and found himself thrust into violence when an armed robber threatened to harm his friend. Cummings defused the situation and de-escalated tensions. Later, one of his friends laughed saying '...that was like a scene out of a movie...' and when Cummings got back to New York he started writing scenes about growing up on napkins outside the door of the bar. Cummings was acting and producing a play in New York when Dave McLaughlin went to visit. The play inspired McGlaughlin so much he stayed up all night and wrote a play of his own. Cummings was impressed with his friend's passion and shared his story with McLaughlin and three weeks later the two guys completed 'Brass Ring'. It wasn't long before the screenplay made its way to film actor and TV star, John Shea. Shea met with Cummings and felt the script was "full of promise". Over the next year, Shea spent time in South Boston with Cummings getting to know the neighborhood, seeing for himself that the world of Southie had its own rules and was truly like no other place he had ever been. He committed to working with the writers on the screenplay and agreed to direct the film. During the next year, Shea worked with them on the script, scouted locations, and pieced the production together while raising the money needed to shoot the film.

The lead role was originally offered to Mark Wahlberg but when Mark landed the lead role in "Boogie Nights", he was catapulted into the movie star he was destined to become. Cummings' younger brother Dan was a huge fan of Donnie Wahlberg who was a star in his own right and the leader of the group "New Kids on the Block". Cummings listened to his little brother and got in touch with Donnie and the two guys hit it off. Cummings called Shea and it didn't take long before Shea realized Wahlberg was born to play the role. At the invitation of Ron Howard, Shea spent a day with Howard in New York as Ron was completing the sound mix on "Ransom" in which Wahlberg had a supporting role. Shea liked what he saw and Wahlberg was offered the role. Cummings worked with Bill McCutchen and Hugh Wilson and the producers raised the financing and the independent film was a go. Shea then offered the lead female role to Rose McGowan and the rest of the cast fell into place.[citation needed]

Shooting was scheduled for February 1997, in the middle of a very cold and brutal Boston winter. The film was shot with a full union crew in twenty-four days. In addition to Donnie Wahlberg in the lead role of Danny Quinn, Rose McGowan was cast in the supporting part as Danny's sister Kathy, as well as Anne Meara in the role as Danny's mother. With James Cummings playing the role of Joey Ward as the film's antagonist. Amanda Peet joined the cast in Boston just before production began. Will Arnet was a friend of Cummings in New York and Anne Meara, a friend of Shea's, agreed to play the key role of the mother of the Quinn clan. Lenny Clarke was cast as Fat Eddie with Steve Sweeney lined up as Peter Binda and Broadway star, Jere Shea as Martin Powers who next in line to head up the Irish Mob in the film rounding out the cast. Amanda Peet played the role of Marianne, Danny's former girlfriend, and veteran character actor Lawrence Tierney was cast as the aging Irish Mafia boss Colie Powers. The filmmakers wanted the real-life quality and chose to cast many local actors right out of the neighborhood: Sue Costello, Bo Cleary, Phil Barrineau, Jere Shea, Robert Wahlberg (Donnie's real older brother), Jay Giannoni, Jeffery Cook, and Steve Koslowski.[citation needed]

Celebrated jazz drummer Johnny Blowers also makes an appearance in The Quencher tavern, "telling Sinatra stories." The film ends as the real St. Patrick's Day parade goes through South Boston. A first, the filmmakers were given permission by Thomas Menino, the Mayor of Boston, to shoot the parade. Directors of photography Allen Baker and Michael Bulter used five 35mm cameras, to capture the Southie neighborhood.

After almost a year of post-production editing and scoring (by composer Wayne Sharp) in New York, the filmmakers changed the film's name to "Southie" at the suggestion of Wahlberg. It was the first feature film ever shot entirely in the old South Boston neighborhood, a place once described as "the last white ghetto in America" and the home of the Irish mafia headed by the controversial James "Whitey" Bulger, called in the film "Colie Powers" and portrayed by Lawrence Tierney in his final screen performance. In 1998 "Southie" won Best Picture (The American Independent Filmmaker Award) at the first festival it entered, The Seattle International Film Festival. It then played to sold-out houses at the Nantucket Film Festival, the AFI Festival in Los Angeles, and was acquired for distribution by Lions Gate Pictures after its screening at the Montreal Festival du Monde where it was the only American film representing the United States in the main competition. In April 1999 it played at the 14th Dublin Film Festival. Critic Padraig Browne wrote in the Irish Times: "Shea directs with a nice lean style and Wahlberg shows that he's every bit as good as his brother, Boogie Nights' Mark."

Film critic Jay Carr of The Boston Globe wrote that the film had "heartfelt urgency" with "an intense individual and communal commitment that seems to boil up from the streets." James Verniere of the Boston Herald gave it three stars and wrote that there were "powerful performances" with an "electric charge especially by leading man Donnie Wahlberg."

The Hollywood Reporter gave the filmmakers praise as it touted the raw talent on display, with Donnie Wahlberg matching brother Mark in terms of macho appeal and unforced naturalism and promising talents of Rose McGowan and James Cummings, who each provided equally vivid performances. the film's director, John Shea has a small role as Danny's cop cousin and underplays nicely.